Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/13—Phenols; Phenolates
  • C08K5/134—Phenols containing ester groups
  • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/13—Phenols; Phenolates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/49—Phosphorus-containing compounds
  • C08K5/51—Phosphorus bound to oxygen
  • C08K5/52—Phosphorus bound to oxygen only
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/49—Phosphorus-containing compounds
  • C08K5/51—Phosphorus bound to oxygen
  • C08K5/52—Phosphorus bound to oxygen only
  • C08K5/527—Cyclic esters

Definitions

• the present invention relates in general to the stabilization of poly-a-olefins against light-induced deterioration and, in particular, to polypropylene compositions so stabilized by the incorporation therein of an effective light stabilizing amount of a combination of (a) n-hexadecyl 3,5-di-t.butyl-4-hydroxybenzoate and (b) a dialkyl pentaerythrityl diphosphite.
• a benzophenone or benzotriazole may be added for improved stability.
• alkyl esters nor the aryl esters of 3,5-di-t.butyl-4-hydroxybenzoic acid are, when used alone, completely satisfactory light stabilizers for .polyolefins, although it is believed that the alkyl esters, particularly the higher alkyl (C 8 -C 20 ), are somewhat superior to the aryl esters.
• the present invention provides light stabilizer compositions, which exhibit enhanced light stability in poly- ⁇ -olefins, comprising a combination of (a) n-hexadecyl 3,5-di-t.butyl-4-hydroxybenzoate and (b) a dialkyl pentaery- thrityl diphosphite compound, represented by the formula: wherein R is an alkyl group containing from about 8 to 20 carbon atoms. Further enhancement of the light stability arises from adding to the above combination a benzophenone or benzotriazole compounds
• the invention provides light stabilizer compositions, as defined, and light stabilized poly-a-olefin co positions containing an effective light stabilizing amount of the light stabilizer composition, as well as a method for stabilizing poly-a-olefins against light-induced degradation by the incorporation therein of an effective light stabilizing amount of the above-defined light stabilizer compositions.
• compositions of the invention provide significantly enhanced light stability to poly-a-olefins, particularly polypropylene, over either component used alone at the same concentration, or over combinations of n-hexadecyl 3,5-di-t.butyl-4-hydroxybenzoate with other known phosphite esters, or over aryl esters of 3,5-di-t.butyl-4-hydroxybenzoic acid with known phosphites, including dialkyl pentaerythrityl diphosphites.
• n-Hexadecyl 3,5-di-t.butyl-4-hydroxybenzoate is a known compound. It may be prepared in accordance with procedures described in U.S. Patent 3,681,431, for the preparation of the n-octadecyl ester, except that n-hexadecanol is used instead-of n-octadecanol.
• dialkyl pentaerythrityl diphosphites are also known compounds and are described in U.S. Patent 3,205,250, particularly column 7, lines 25-43, and in Examples 9-13 therein.
• the preferred dialkyl pentaerythrityl diphosphites contain C 8 -C 20 alkyl groups, and most preferably contain C 12 -C 20 alkyl groups, representative of which are diisodecyl pentaerythrityl diphosphite, distearyl pentaerythrityl diphosphite, dilauryl pentaerythrityl diphosphite, and the like.
• Distearyl pentaerythrityl diphosphite available commercially as Weston 618 (Weston Chem. Co.) is the most preferred diphosphite.
• effective stabilization of the polyolefin is achieved by the incorporation therein of about 0.1 to 2 percent by weight of the light stabilizer combination of the invention and preferably from about 0.25 to about 1 percent by weight.
• the weight ratio of the n-hexadecyl ester of 3,5--di-t.butyl-4-hydroxybenzoic acid to the dialkyl pentaery- thrityl diphosphite in the light stabilizer combination will preferably be such as to minimize the amount of the phosphite ester. In general, however, effective weight ratios will vary between about 1:1 to about 5:1 (ester:phosphite).
• the benzophenone or benzotriazole when used, are used in amounts of about 0.1 to 1 percent by weight.
• the stabilizer composition of the invention may also contain a benzophenone or benzotriazole light stabilizer to provide further enhancement of activity.
• the benzophenone or benzotriazole may be added in an amount of from about 0.1 to 1 percent by weight, based on the weight of the polymer, with the ratio of n-hexadecyl ester to benzophenone or benzotriazole being about 1/1 to 5/1.
• Representative benzophenones include 2-hydroxy-4-octyloxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2-hydroxy-4-n-hexyloxy- benzophenone, 2-hydroxy-4-methoxybenzophenone, 2,2'-dihydroxy--4,4'-dimethoxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, and the like; representative benzotriazoles include 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(3'-tert.butyl--2'-hydroxy-5'-methylphenyl)-5-chlorobenzotriazole, 2-(3',5'--di-tert.butyl-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-tert.octylphenyl)benzotriazole, 2-(3',5'-di-tert.amyl-2
• the polyolefins stabilized in accordance with the invention are poly-a-olefins, particularly polypropylene, and include low and high density polyethylene, polybutylene, and copolymers of ethylene and propylene and ethylene and butylene, and the like.
• the stabilizer composition may be incorporated into the polyolefin by any of the means well-known in the art for such purpose, including dry blending of the additive with the polyolefin in powder or granular form, followed by milling, Banbury mixing, molding, casting, etc.
• the compositions may include other stabilizers, such as thermal processing anti oxidants, lubricants, fillers, pigments and dyes, antistatic agents, and the like.
• thermal processing antioxidants which may be used alone or in combinations are used in conventional effective amounts, i.e. up to about 2 percent by weight.
• Suitable compounds include such as:
• Unstabilized powdered polypropylene (Profax 6401-Hercules; 100 parts by weight was dry blended with two thermal processing antioxidants (0.05 part by weight of 2,6-di-t. butyl-4-methyl phenol and 0.05 part by weight of n-octadecyl 3,5-di-t.butyl-4-hydroxyhydrocinnamate) 0.1 part by weight of calcium stearate, and the light stabilizers shown in the accompanying table.
• the compositions were then extruded at a maximum extrusion temperature of 440°F and pelletized.
• the pellets were then extruded into fibers at a maximum temperature of 485°F using a draw ratio of 7/1.
• the fibers were exposed to a Xenon arc in a Weather-O-Meter and periodically tested for tensile (break) strength.
• the data shown in the table represent the time in hours for the fiber to lose 50% of its original tensile (break) strength.
• the data show the unexpected enhancement of light stabilization by the combination of the invention (d) over 'either component alone (b) and (c), as well as over the aryl ester alone (e) or in combination with distearyl pentaery- thrityl diphosphite (f).

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1978
  • 1978-10-13 US US05/951,230 patent/US4237042A/en not_active Expired - Lifetime
• 1979
  • 1979-08-10 CA CA333,507A patent/CA1111238A/fr not_active Expired
  • 1979-08-16 AU AU49986/79A patent/AU526749B2/en not_active Ceased
  • 1979-08-17 AT AT79301686T patent/ATE4993T1/de active
  • 1979-08-17 EP EP79301686A patent/EP0010346B1/fr not_active Expired
  • 1979-08-17 DE DE7979301686T patent/DE2966299D1/de not_active Expired
  • 1979-09-25 BR BR7906130A patent/BR7906130A/pt unknown
  • 1979-10-11 JP JP13009279A patent/JPS5554339A/ja active Granted

Patent Citations (4)

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